Madonna Dated Tupac, But He's Not The Only Surprising Celeb Her Madgesty Had A Relationship With

Oh, Madonna. What are we gonna do with you? Even though the 56-year-old Rebel Heart singer has been in the blinding bright spotlight ever since her career began more than three decades ago, she’s still managed to keep some secrets close to her chest. On Howard Stern on Wednesday, the shock-jock asked her why she was ornery in an interview with David Letterman in 1994, and Madonna said she was feeling “gangsta” at the time. Why? Because Madonna was dating Tupac Shakur. WTF?!Although at first it’s tough to imagine Madonna dating the iconic West Coast rapper, she’s had a long, strange dating history as varied as her career itself. Some of her more well-known paramours include Sean Penn and her longtime husband, director Guy Ritchie who she was married to from 2000 to 2008. But she's had some lesser known and even more interesting relationships and affairs. Here are some of Madonna’s most bizarre trysts that you might not know about.

Dennis Rodman — 1994


Even though now the former basketball player/kook Rodman’s heart seems to belong to Kim Jong Un, he and Madonna dated briefly in 1994 at the height of both their wacky fashion. Rodman was not so pleased with the relationship looking back at it. “I didn’t know what the hell this white megastar wanted from me,” he wrote in his autobiography. Well, she’s still a megastar, so who’s laughing now, Rodman?

Jean Michel Basquiat — The '80s

Pascal Le Segretain/Getty Images Entertainment/Getty Images

In the early '80s, Madonna dated famous New York street artist Jean Michel Basquiat. She told Us Magazine in December 2014 that she admired the artist so much for his passion and the way he poured his heart into his work, but said he was “too fragile for this world.” Sob.

Vanilla Ice — 1992

Mike Coppola/Getty Images Entertainment/Getty Images

Though they dated for eight months, Vanilla Ice apparently broke up with Madonna because she printed the Sex Book in 1992, which he called a “slutty package.” Then when the book came out I was so embarrassed and ashamed. It was a porno,” he told NY Daily News. Damn, that’s cold as Ice.

Image: madonnaciccone/Tumblr

John F. Kennedy, Jr. — 1987


Talk about scandalous. According to Christopher Andersen’s biography of the late JFK, Jr., the two had an affair while Madonna was still dating Sean Penn. Sounds not unlike the JFK/Marilyn Monroe affair…

John "Jellybean" Benitez — 1983 - 1985

George De Sota/Getty Images Entertainment/Getty Images

Even though many people might not know who DJ John “Jellybean” Benitez is, he had to be included on this list because his nickname is Jellybean. He helped Madonna start her career, producing and remixing many of her early singles, including the great “Holiday.”

Alex Rodriguez — 2008


To be fair, this one is a rumor, but the Yankee star’s wife Cynthia supposedly left him after she suspected an affair between her husband and Madonna when he became intensely interested in Kaballah. Even if they weren’t having an affair, it was probably good for Cynthia to get out of there.